EP0863702B1 - Fungicidal mixture - Google Patents
Fungicidal mixture Download PDFInfo
- Publication number
- EP0863702B1 EP0863702B1 EP96939086A EP96939086A EP0863702B1 EP 0863702 B1 EP0863702 B1 EP 0863702B1 EP 96939086 A EP96939086 A EP 96939086A EP 96939086 A EP96939086 A EP 96939086A EP 0863702 B1 EP0863702 B1 EP 0863702B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- alkoxy
- choch
- och
- haloalkoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 0 *C=C(C(*)=O)c(cccc1)c1Oc1cc(Oc2ccccc2*)ncn1 Chemical compound *C=C(C(*)=O)c(cccc1)c1Oc1cc(Oc2ccccc2*)ncn1 0.000 description 3
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
Definitions
- the compounds of the formula I according to Table I.1 are preferably suitable for the mixtures according to the invention.
- the active ingredients IIA and IIB are described, for example, in the following documents: EP-A 178 826, EP-A 203 606, EP-A 203 608, EP-A 206 523, EP-A 212 859, EP-A 226 917, EP-A 229 974, EP-A 242 070, EP-A 242 081, EP-A 243 012, EP-A 243 014, EP-A 251 082, EP-A 253 213, EP-A 254 426, EP- A 256 667, EP-A 260 794, EP-A 260 832, EP-A 267 734, EP-A 273 572, EP-A 274 825, EP-A 278 595, EP-A 280 185, EP-A 291 196, EP-A 299 694, EP-A 307 101, EP-A 307 103, EP-A 310 954, EP-A 312 221, EP-A 312 243, EP-A 329 011, EP-A 331 9
- the present invention was based on the object, the fungicidal Effect of the compounds I by mixing with suitable other fungicides.
- (het) aryl group has the following meaning No. if necessary subst.
- (Het) aryl literature II.2B-1 C 6 H 5 EP-A 253 213 II.2B-2 6- [2-CN-C 6 H 4 -O] pyrimidin-4-yl
- (Het) aryl group has the following meaning No. if necessary subst.
- Q is phenyl
- n is
- (het) aryl group has the following meaning No. if necessary subst.
- the mixtures of the compounds I and IIA or IIB or the simultaneous joint or separate use of the connections I and IIA or I and IIB are excellent Action against a wide range especially of phytopathogenic fungi. They are partly systemically effective (i.e. when used for crop protection without Loss of effectiveness absorbed by the treated plant and possibly transported in the plant) and can therefore also can be used as leaf and soil fungicides.
- Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Puccinia species on cereals, Rhizoctonia species on cotton, rice and Lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species Cereals, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae Rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudo
- the compounds I and IIA or I and IIB can simultaneously, namely applied together or separately or in succession be, the order in separate application in generally has no effect on the success of the control.
- the compounds I and IIA are usually in one Weight ratio of 10: 1 to 1:20, preferably 5: 1 to 1: 3, in particular 3: 1 to 1: 1 (I: IIA) applied.
- the compounds I and IIB are usually in one Weight ratio of 10: 1 to 1:20, preferably 5: 1 to 1: 3, in particular 3: 1 to 1: 1 (I: IIB) applied.
- the application rates of the mixtures according to the invention depend on the nature of the desired effect at 0.015 to 10 kg / ha, preferably 0.1 to 7 kg / ha, in particular 0.2 to 3 kg / ha.
- the application rates for the compounds I are 0.005 up to 3 kg / ha, preferably 0.02 to 2 kg / ha, in particular 0.05 to 1 kg / ha.
- the application rates for the compounds IIA are in general at 0.005 to 5 kg / ha, preferably 0.01 to 2 kg / ha, in particular 0.01 to 1 kg / ha.
- the application rates for the compounds IIB are in general at 0.005 to 5 kg / ha, preferably 0.01 to 2 kg / ha, in particular 0.01 to 1 kg / ha.
- application rates are generally applied on a mixture of 0.001 to 0.1 g / kg of seed, preferably 0.002 up to 0.05 g / kg of seed, in particular 0.005 to 0.5 g / kg of seed used.
- pathogenic harmful fungi are to be combated for plants the joint or separate application of the connections I and IIA or I and IIB or the mixtures of the compounds I and IIA or I and IIB by spraying or dusting the Seeds, plants or soils before or after sowing the plants or before or after the plants germinate.
- the fungicidal synergistic mixtures or the compounds I and IIA or I and IIB can for example in the form of directly sprayable solutions, powders and suspensions or in the form of high-proof aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, Pastes, dusts, spreading agents or granules prepared and by spraying, atomizing, dusting, scattering or Pouring can be applied.
- the form of application depends on Usage; in any case, it should be as fine and ensure uniform distribution of the mixture according to the invention.
- the formulations are prepared in a manner known per se, e.g. by adding solvents and / or carriers.
- the formulations are usually inert additives such as emulsifiers or dispersants.
- alkali, alkaline earth and ammonium salts of aromatic sulfonic acids e.g. Lignin-, Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acid, alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenol or tributylphenyl polyglycol
- Powders, materials for spreading and dusts can be mixed or combined Grinding of the compounds I and IIA or I and IIB or the mixtures of the compounds I and IIA or I and IIB with a solid carrier.
- Granules are usually by binding the active ingredient or the active ingredients are produced on a solid carrier.
- Mineral soils such as silica gel, silicas, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as flour, tree bark, wood and nutshell flour, Cellulose powder and other solid carriers.
- Mineral soils such as silica gel, silicas, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as flour, tree
- the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of one of the compounds IA or IB, IIA or IIB or the mixture of the compounds I and IIA or I and IIB.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to 1 H-NMR or HPLC spectrum).
- the compounds I, IIA and IIB or the mixtures or the corresponding formulations are applied by the Harmful fungi, their habitat or those to be protected against fungal attack Materials, plants, seeds, soils, surfaces or spaces with a fungicidally effective amount of the mixture or compounds I and IIA or I and IIB when applied separately. Treatment can take place before or after infestation by the harmful fungi respectively.
- Pepper seedlings of the variety "Neusiedler Ideal Elite" were after 4 to 5 leaves had developed well, with watery ones Suspensions containing 80% active ingredient and 20% emulsifier in the Contained dry substance, sprayed to runoff. After drying of the spray coating, the plants were exposed to a conidia of the fungus Botrytis cinerea and sprayed at 22 to 24 ° C in a chamber with high humidity. To The disease had remained on the untreated control plants for 5 days developed so strongly that the resulting leaf necrosis covered most of the leaves.
- Efficiency of the individual active ingredients Active ingredient Active substance concentration in the spray mixture [ppm] Efficiency [% of the untreated control] (A) 100 84 25th 40 (B) 100 80 25th 65 (C) 100 70 25th 35 (D) 25th 0 (E) 25th 0 (F) 25th 0 Efficiency of the mixture Active ingredient mixture observed efficiency expected efficiency 100 ppm (A) + 25 ppm (D); Mixing ratio 4: 1 100 100 84 84 25 ppm (A) + 25 ppm (D); Mixing ratio 1: 1 92 40 100 ppm (A) + 25 ppm (E); Mixing ratio 4: 1 99 84 25 ppm (A) + 25 ppm (E); Mixing ratio 1: 1 83 40 100 ppm (A) + 25 ppm (P); Mixing ratio 4: 1 98 84 25 ppm (A) + 25 ppm (F); Mixing ratio 1: 1 99 40 40 100 ppm (B) + 25 ppm (D); Mixing ratio 4: 1
- Test result The observed efficiency is in all Mixing ratios higher than calculated using the Colby formula.
- Efficiency of the individual active ingredients Active ingredient Active substance concentration in the spray mixture [ppm] Efficiency [% of the untreated control] (A) 100 20th (B) 100 25th 25th 10th (C) 100 25th 25th 30th (D) 25th 77 (F) 25th 10th Efficiency of the mixture Active ingredient mixture observed efficiency expected efficiency 100 ppm (A) + 25 ppm (F); Mixing ratio 4: 1 77 48 25 ppm (B) + 25 ppm (D); Mixing ratio 1: 1 90 79 100 ppm (B) + 25 ppm (F); Mixing ratio 4: 1 80 51 25 ppm (B) + 25 ppm (F); Mixing ratio 1: 1 75 42 100 ppm (C) + 25 ppm (F); Mixing ratio 4: 1 97 51 25 ppm (C) + 25 ppm (F); Mixing ratio 1 89 55
- Test result The observed efficiency is in all Mixing ratios higher than calculated using the Colby formula.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft eine fungizide Mischung,
enthaltend
- R1
- Wasserstoff, C1-C8-Alkyl, welches partiell oder vollständig
halogeniert sein und/oder eine oder zwei der
folgenden Gruppen tragen kann: C1-C4-Alkoxy, C1-C4-Halogenalkoxy,
C1-C4-Alkylthio, C3-C7-Cycloalkyl,
C5-C7-Cycloalkenyl, wobei die cyclischen Gruppen ihrerseits
ein bis drei Halogenatome, C1-C3-Alkylgruppen
und/oder C1-C3-Alkoxygruppen tragen können und Aryl,
welches partiell oder vollständig halogeniert sein
und/oder einen bis drei der folgenden Substituenten
tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogen-alkyl,
C1-C4-Alkoxy, C1-C4-Halogenalkoxy und C1-C4-Alkylthio;
C3-C6-Cycloalkyl oder C3-C6-Cycloalkenyl, wobei diese Reste partiell oder vollständig halogeniert sein und/oder eine bis fünf der folgenden Gruppen tragen können: C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und Aryl, welches partiell oder vollständig halogeniert sein und/oder einen bis drei der folgenden Substituenten tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und C1-C4-Alkylthio;
C6-C15-Bicycloalkyl oder C7-C15-Bicycloalkenyl, wobei diese Reste partiell oder vollständig halogeniert sein und/oder eine bis fünf der folgenden Gruppen tragen können: C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und Aryl, welches partiell oder vollständig halogeniert sein und/oder einen bis drei der folgenden Substituenten tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und C1-C4-Alkylthio; - R2 und R3
- unabhängig voneinander Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;
- z
- H oder R4-(CO)-, wobei
- R4
- C1-C6-Alkyl oder C2-C6-Alkenyl, wobei diese Gruppen
partiell oder vollständig halogeniert sein und/oder
einen der folgenden Reste tragen können:
C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio,
C3-C7-Cycloalkyl, C5-C7-Cycloalkenyl oder Aryl, wobei
die aromatischen Reste ihrerseits eine bis drei
der folgenden Gruppen tragen können: Nitro, Cyano,
Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy,
C1-C4-Halogenalkoxy und C1-C4-Alkylthio;
C3-C7-Cycloalkyl oder C5-C7-Cycloalkenyl, wobei diese Gruppen ein bis drei der folgenden Reste tragen können: Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl und C1-C4-Alkoxy;
Aryl, welches partiell oder vollständig halogeniert sein und/oder ein bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und C1-C4-Alkylthio;
OR5 oder NR6R7, wobei- R5
- C1-C6-Alkyl oder C2-C6-Alkenyl bedeutet, wobei
diese Gruppen partiell oder vollständig halogeniert
sein und/oder einen der folgenden Reste
tragen können: C1-C4-Alkoxy, C1-C4-Halogenalkoxy,
C1-C4-Alkylthio, C3-C7-Cycloalkyl, C5-C7-Cycloalkenyl
oder Aryl, wobei die aromatischen
Reste ihrerseits eine bis drei der folgenden
Gruppen tragen können: Nitro, Cyano, Halogen,
C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy,
C1-C4-Halogenalkoxy und C1-C4-Alkylthio;
C3-C7-Cycloalkyl oder C5-C7-Cyencloalkenyl bedeutet, wobei diese Gruppen einen bis drei der folgenden Reste tragen können: Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl und C1-C4-Alkoxy;
Aryl, welches partiell oder vollständig halogeniert sein und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und C1-C4-Alkylthio; - R6
- C1-C6-Alkyl oder C2-C6-Alkenyl, wobei diese
Gruppen partiell oder vollständig halogeniert
sein und/oder einen der folgenden Reste tragen
können: C1-C4-Alkylthio C3-C7-Cycloalkyl, C5-C7-Cycloalkenyl
oder Aryl, wobei die aromatischen
Reste ihrerseits eine bis drei der folgenden
Gruppen tragen können: Nitro, Cyano, Halogen,
C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy,
C1-C4-Halogenalkoxy und C1-C4-Alkylthio;
C3-C7-Cycloalkyl oder C5-C7-Cycloalkenyl bedeutet, wobei diese Gruppen ein bis drei der folgenden Reste tragen können: Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl und C1-C4-Alkoxy;
Aryl, welches partiell oder vollständig halogeniert sein und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy und C1-C4-Alkylthio; und - R7
- Wasserstoff oder C1-C6-Alkyl,
- R'
- -C[CO2CH3]=CHOCH3, -C[CO2CH3]=NOCH3, -C[COMHCH3]=NOCH3, -C[CO2CH3]=CHCH3, -C[CO2CH3]=CHCH2CH3, -C[COCH3]NOCH3, -C[COCH2CH3]=NOCH3, -N(OCH3)-CO2CH3, -N(CH3)-CO2CH3, -N(CH2CH3)-CO2CH3;
- R"
- ein C-organischer Rest, welcher direkt oder über eine
Oxy-, Mercapto-, Amino-, oder Alkylaminogruppe gebunden
ist;
zusammen mit einer Gruppe X und dem Ring Q bzw. T, an den sie gebunden sind, ein ggf. subst. bicyclisches, partiell oder vollständig ungesättigtes System, welches neben Kohlenstoffringgliedern Heteroatome aus der Gruppe Sauerstoff, Schwefel und Stickstoff enthalten kann; - Rx
- -OC[CO2CH3]=CHOCH3, -OC[CO2CH3]=CHCH3, -OC[CO2CH3]=CHCH2CH3, -SC[CO2CH3]=CHOCH3, -SC[CO2CH3]=CHCH3, -SC[CO2CH3]=CHCH2CH3, -N(CH3)C[CO2CH3]=CHOCH3, -N(CH3)C(CO2CH3]=NOCH3, -CH2C[CO2CH3]=CHOCH3, -CH2C[CO2CH3]=NOCH3. -CH2C[CONHCH3]=NOCH3;
- Ry
- Sauerstoff, Schwefel, =CH- oder =N-;
- n
- 0, 1, 2 oder 3, wobei die Reste X verschieden sein können, wenn n > 1 ist;
- X
- Cyano, Nitro, Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl,
C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio;
für den Fall, daß n > 1 ist, eine an zwei benachbarte C-Atome des Phenylrings gebundene C3-C5-Alkylen-, C3-C5-Alkenylen-, Oxy-C2-C4-alkylen-, Oxy-C1-C3-alkylenoxy-, Oxy-C2-C4-alkenylen-, Oxy-C2-C4-alkenylenoxy- oder Butadiendiylgruppe, wobei diese Ketten ihrerseits ein bis drei der folgenden Reste tragen können: Halogen, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkylthio; - Y
- =C- oder -N-;
- Q
- Phenyl, Pyrrolyl, Thienyl, Furyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Thiadiazolyl, Triazolyl, Pyridinyl, 2-Pyridinyl, Pyrimidinyl und Triazinyl;
- T
- Phenyl, Oxazolyl, Thiazolyl, Thiadiazolyl, Oxadiazolyl, Pyridinyl, Pyrimidinyl und Triazinyl,
- R 1
- Hydrogen, C 1 -C 8 alkyl, which can be partially or completely halogenated and / or can carry one or two of the following groups: C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 - Alkylthio, C 3 -C 7 cycloalkyl, C 5 -C 7 cycloalkenyl, where the cyclic groups in turn can carry one to three halogen atoms, C 1 -C 3 alkyl groups and / or C 1 -C 3 alkoxy groups and aryl, which be partially or fully halogenated and / or may carry one to three of the following substituents: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 -halogen-alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkenyl, these radicals being partially or completely halogenated and / or bearing one to five of the following groups: C 1 -C 4 alkyl, C 1 -C 4 - Haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and aryl, which can be partially or completely halogenated and / or can carry one to three of the following substituents: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
C 6 -C 15 bicycloalkyl or C 7 -C 15 bicycloalkenyl, these radicals being partially or completely halogenated and / or bearing one to five of the following groups: C 1 -C 4 alkyl, C 1 -C 4 - Haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and aryl, which can be partially or completely halogenated and / or can carry one to three of the following substituents: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio; - R 2 and R 3
- independently of one another halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
- e.g.
- H or R 4 - (CO) -, where
- R 4
- C 1 -C 6 alkyl or C 2 -C 6 alkenyl, these groups being partially or completely halogenated and / or bearing one of the following radicals: C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 3 -C 7 cycloalkyl, C 5 -C 7 cycloalkenyl or aryl, where the aromatic radicals can in turn carry one to three of the following groups: nitro, cyano, halogen, C 1 -C 4- alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, where these groups can carry one to three of the following radicals: halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 -C 4 alkoxy;
Aryl which can be partially or fully halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
OR 5 or NR 6 R 7 , where- R 5
- C 1 -C 6 alkyl or C 2 -C 6 alkenyl, where these groups are partially or completely halogenated and / or can carry one of the following radicals: C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy , C 1 -C 4 alkylthio, C 3 -C 7 cycloalkyl, C 5 -C 7 cycloalkenyl or aryl, where the aromatic radicals can in turn carry one to three of the following groups: nitro, cyano, halogen, C 1 - C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
C 3 -C 7 cycloalkyl or C 5 -C 7 cyencloalkenyl, where these groups can carry one to three of the following radicals: halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 - C 4 alkoxy;
Aryl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio; - R 6
- C 1 -C 6 alkyl or C 2 -C 6 alkenyl, these groups being partially or completely halogenated and / or bearing one of the following radicals: C 1 -C 4 alkylthio C 3 -C 7 cycloalkyl, C 5 -C 7 cycloalkenyl or aryl, where the aromatic radicals can in turn carry one to three of the following groups: nitro, cyano, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 Alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio;
C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, where these groups can carry one to three of the following radicals: halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl and C 1 - C 4 alkoxy;
Aryl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy and C 1 -C 4 alkylthio; and - R 7
- Hydrogen or C 1 -C 6 alkyl,
- R '
- -C [CO 2 CH 3 ] = CHOCH 3 , -C [CO 2 CH 3 ] = NOCH 3 , -C [COMHCH 3 ] = NOCH 3 , -C [CO 2 CH 3 ] = CHCH 3 , -C [CO 2 CH 3 ] = CHCH 2 CH 3 , -C [COCH 3 ] NOCH 3 , -C [COCH 2 CH 3 ] = NOCH 3 , -N (OCH 3 ) -CO 2 CH 3 , -N (CH 3 ) - CO 2 CH 3 , -N (CH 2 CH 3 ) -CO 2 CH 3 ;
- R "
- a C-organic radical which is bonded directly or via an oxy, mercapto, amino or alkylamino group;
together with a group X and the ring Q or T to which they are attached, a subst. bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen; - R x
- -OC [CO 2 CH 3 ] = CHOCH 3 , -OC [CO 2 CH 3 ] = CHCH 3 , -OC [CO 2 CH 3 ] = CHCH 2 CH 3 , -SC [CO 2 CH 3 ] = CHOCH 3 , -SC [CO 2 CH 3 ] = CHCH 3 , -SC [CO 2 CH 3 ] = CHCH 2 CH 3 , -N (CH 3 ) C [CO 2 CH 3 ] = CHOCH 3 , -N (CH 3 ) C (CO 2 CH 3 ] = NOCH 3 , -CH 2 C [CO 2 CH 3 ] = CHOCH 3 , -CH 2 C [CO 2 CH 3 ] = NOCH 3. -CH 2 C [CONHCH 3 ] = NOCH 3 ;
- R y
- Oxygen, sulfur, = CH- or = N-;
- n
- 0, 1, 2 or 3, where the radicals X can be different if n is>1;
- X
- Cyano, nitro, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio;
in the event that n> 1, a C 3 -C 5 alkylene, C 3 -C 5 alkenylene, oxy-C 2 -C 4 alkylene, oxy bonded to two adjacent C atoms of the phenyl ring -C 1 -C 3 -alkyleneoxy, oxy-C 2 -C 4 -alkenylene, oxy-C 2 -C 4 -alkenyleneoxy or butadienediyl group, where these chains can in turn carry one to three of the following radicals: halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkylthio; - Y
- = C- or -N-;
- Q
- Phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridinyl, pyrimidinyl and triazinyl;
- T
- Phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl and triazinyl,
Verbindungen der Formel I sind bekannt aus EP-A 339 418, EP-A 653 417, EP-A 653 418 und den deutschen Patentanmeldungen Az. 195 04 599.8 und 195 40 970.1.Compounds of the formula I are known from EP-A 339 418, EP-A 653 417, EP-A 653 418 and the German patent applications Ref. 195 04 599.8 and 195 40 970.1.
Vorzugsweise kommen für die erfindungsgemäßen Mischungen die
Verbindungen der Formel I gemäß Tabelle I.1 in Betracht.
Besonders bevorzugt sind Verbindungen der Formel I gemäß
Tabelle I.2.
Die Wirkstoffe IIA und IIB sind beispielsweise in den folgenden
Schriften beschrieben: EP-A 178 826, EP-A 203 606, EP-A 203 608,
EP-A 206 523, EP-A 212 859, EP-A 226 917,
EP-A 229 974, EP-A 242 070, EP-A 242 081, EP-A 243 012,
EP-A 243 014, EP-A 251 082, EP-A 253 213, EP-A 254 426,
EP-A 256 667, EP-A 260 794, EP-A 260 832, EP-A 267 734,
EP-A 273 572, EP-A 274 825, EP-A 278 595, EP-A 280 185,
EP-A 291 196, EP-A 299 694, EP-A 307 101, EP-A 307 103,
EP-A 310 954, EP-A 312 221, EP-A 312 243, EP-A 329 011,
EP-A 331 966, EP-A 335 519, EP-A 336 211, EP-A 337 211,
EP-A 341 845, EP-A 350 691, EP-A 354 571, EP-A 363 818,
EP-A 370 629, EP-A 373 775, EP-A 374 811, EP-A 378 308,
EP-A 378 755, EP-A 379 098, EP-A 382 375, EP-A 383 117,
EP-A 384 211, EP-A 385 224, EP-A 385 357, EP-A 386 561,
EP-A 386 681, EP-A 389 901, EP-A 391 451, EP-A 393 428,
EP-A 393 861, EP-A 398 692, EP-A 400 417, EP-A 402 246,
EP-A 405 782, EP-A 407 873, EP-A 409 369, EP-A 414 153,
EP-A 416 746, EP-A 420 091, EP-A 422 597, EP-A 426 460,
EP-A 429 968, EP-A 430 471, EP-A 433 233, EP-A 433 899,
EP-A 439 785, EP-A 459 285, EP-A 460 575, EP-A 463 488,
EP-A 463 513, EP-A 464 381, EP-A 468 684, EP-A 468 695,
EP-A 468 775, EP-A 471 261, EP-A 472 224, EP-A 472 300,
EP-A 474 042, EP-A 475 158, EP-A 477 631, EP-A 480 795,
EP-A 483 851, EP-A 483 985, EP-A 487 409, EP-A 493 711,
EP-A 498 188, EP-A 498 396, EP-A 499 823, EP-A 503 436,
EP-A 508 901, EP-A 509 857, EP-A 513 580, EP-A 515 901,
EP-A 517 301, EP-A 528 245, EP-A 532 022, EP-A 532 126,
EP-A 532 127, EP-A 535 980, EP-A 538 097, EP-A 544 587,
EP-A 546 387, EP-A 548 650, EP-A 564 928, EP-A 566 455,
EP-A 567 828, EP-A 571 326, EP-A 579 071, EP-A 579 124,
EP-A 579 908, EP-A 581 095, EP-A 582 902, EP-A 582 925,
EP-A 583 806, EP-A 584 625, EP-A 585 751, EP-A 590 610,
EP-A 596 254, WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487,
WO-A 92/18,494, WO-A 92/21,653, WO-A 93/07,116, WO-A 93/08,180,
WO-A 93/08,183, WO-A 93/15,046, WO-A 93/16,986, WO-A 94/00,436,
WO-A 94/05,626, WO-A 94/08,948, WO-A 94/08,968, WO-A 94/10,159,
WO-A 94/11,334, JP-A 02/121,970, JP-A 04/182,461,
JP-A 05/201,946, JP-A 05/201,980, JP-A 05/255,012,
JP-A 05/294,948, JP-A 06/025,133, JP-A 06/025,142,
JP-A 06/056,756, FR-A 2 670 781, GB-A 2 210 041, GB-A 2 218 702,
GB-A 2 238 308, GB-A 2 249 092, GB-A 2 253 624, GB-A 2 255 092,
DE-A 39 05 911, DE Pat. Anm. 43 05 502.8,
DE Pat. Anm. 43 10 143.7, DE Pat. Anm. 43 18 397.2,
DE Pat. Anm. 43 34 709.6, DE Pat. Anm. 44 03 446.6,
DE Pat. Anm. 44 03 447.4, DE Pat. Anm. 44 03 448.2,
DE Pat. Anm. 44 10 424.3, DE Pat. Anm. 44 21 180.5,
DE Pat. Anm. 44 21 182.1, DE Pat. Anm. 44 15 483.6,
DE Pat. Anm. 44 23 615.8 und DE Pat. Anm. 44 23 612.3.The active ingredients IIA and IIB are described, for example, in the following documents: EP-A 178 826, EP-A 203 606, EP-A 203 608, EP-A 206 523, EP-A 212 859, EP-A 226 917,
EP-A 229 974, EP-A 242 070, EP-A 242 081, EP-A 243 012, EP-A 243 014, EP-A 251 082, EP-A 253 213, EP-A 254 426, EP- A 256 667, EP-A 260 794, EP-A 260 832, EP-A 267 734, EP-A 273 572, EP-A 274 825, EP-A 278 595, EP-A 280 185, EP-A 291 196, EP-A 299 694, EP-A 307 101, EP-A 307 103, EP-A 310 954, EP-A 312 221, EP-A 312 243, EP-A 329 011, EP-A 331 966, EP-A 335 519, EP-A 336 211, EP-A 337 211, EP-A 341 845, EP-A 350 691, EP-A 354 571, EP-A 363 818, EP-A 370 629, EP- A 373 775, EP-A 374 811, EP-A 378 308, EP-A 378 755, EP-A 379 098, EP-A 382 375, EP-A 383 117, EP-A 384 211, EP-A 385 224, EP-A 385 357, EP-A 386 561, EP-A 386 681, EP-A 389 901, EP-A 391 451, EP-A 393 428, EP-A 393 861, EP-A 398 692, EP-A 400 417, EP-A 402 246, EP-A 405 782, EP-A 407 873, EP-A 409 369, EP-A 414 153, EP-A 416 746, EP-A 420 091, EP- A 422 597, EP-A 426 460, EP-A 429 968, EP-A 430 471, EP-A 433 233, EP-A 433 899, EP-A 439 785, EP-A 459 285, EP-A 460 575, EP-A 463 488, EP-A 463 513, EP-A 464 381, EP-A 468 684, EP-A 4 68 695, EP-A 468 775, EP-A 471 261, EP-A 472 224, EP-A 472 300, EP-A 474 042, EP-A 475 158, EP-A 477 631, EP-A 480 795 , EP-A 483 851, EP-A 483 985, EP-A 487 409, EP-A 493 711, EP-A 498 188, EP-A 498 396, EP-A 499 823, EP-A 503 436, EP -A 508 901, EP-A 509 857, EP-A 513 580, EP-A 515 901, EP-A 517 301, EP-A 528 245, EP-A 532 022, EP-A 532 126, EP-A 532 127, EP-A 535 980, EP-A 538 097, EP-A 544 587, EP-A 546 387, EP-A 548 650, EP-A 564 928, EP-A 566 455, EP-A 567 828 , EP-A 571 326, EP-A 579 071, EP-A 579 124, EP-A 579 908, EP-A 581 095, EP-A 582 902, EP-A 582 925, EP-A 583 806, EP -A 584 625, EP-A 585 751, EP-A 590 610, EP-A 596 254, WO-A 90 / 07,493, WO-A 92 / 13,830, WO-A 92 / 18,487, WO-A 92 / 18,494 , WO-A 92 / 21,653, WO-A 93 / 07,116, WO-A 93 / 08,180, WO-A 93 / 08,183, WO-A 93 / 15,046, WO-A 93 / 16,986, WO-A 94 / 00,436, WO-A 94 / 05,626, WO-A 94 / 08,948, WO-A 94 / 08,968, WO-A 94 / 10,159, WO-A 94 / 11,334, JP-A 02 / 121,970, JP-A 04 / 182,461, JP -A 05 / 201,946, JP-A 05 / 201,980, JP-A 05 / 255,012, JP-A 05 / 294,948, JP-A 06 / 025,133, JP-A 06 / 025,142, JP-A 06 / 056,756, FR-A 2 670 781, GB-A 2 210 041, GB-A 2 218 702, GB-A 2 238 308, GB-A 2 249 092, GB-A 2 253 624, GB-A 2 255 092, DE-A 39 05 911, DE Pat. Note 43 05 502.8, DE Pat. Note 43 10 143.7, DE Pat. Note 43 18 397.2 , DE Pat. Note 43 34 709.6, DE Pat. Note 44 03 446.6, DE Pat. Note 44 03 447.4, DE Pat. Note 44 03 448.2, DE Pat. Note 44 10 424.3, DE Pat. Note 44 21 180.5, DE Pat. Note 44 21 182.1, DE Pat. Note 44 15 483.6, DE Pat. Note 44 23 615.8 and DE Pat. Note 44 23 612.3.
In den nachveröffentlichten Schriften WO-A 96/24,249 und EP-A 707 792 werden fungizide Mischungen von Verbindungen der Formel I mit anderen Fungiziden, bzw. eines Hydroxyanilinderivates der Formel I mit zwei Methoxyiminophenylacetamidderivaten der Formel IIA beschrieben.In the subsequently published documents WO-A 96 / 24,249 and EP-A 707 792 describes fungicidal mixtures of compounds of Formula I with other fungicides, or a hydroxyaniline derivative of formula I with two methoxyiminophenylacetamide derivatives Formula IIA described.
Der vorliegenden Erfindung lag die Aufgabe zugrunde, die fungizide Wirkung der Verbindungen I durch Mischen mit geeigneten anderen Fungiziden zu steigern.The present invention was based on the object, the fungicidal Effect of the compounds I by mixing with suitable other fungicides.
Demgemäß wurde gefunden, daß sich Schadpilze grundsätzlich besser bekämpfen lassen, wenn man neben einem Wirkstoff I einen weiteren Wirkstoff der Formel IIA oder der Formel IIB anwendet.Accordingly, it was found that harmful fungi are fundamentally better combat if one next to an active ingredient I another Active ingredient of formula IIA or formula IIB applies.
Durch die erfindungsgemäße Kombination der Wirkstoffe I und IIA bzw. IIB wird eine effektivere Bekämpfung des Schadpilzes erreicht, da geringere Aufwandmengen an den Einzelwirkstoffen erforderlich sind (Synergismus).The combination of active ingredients I and IIA according to the invention or IIB will be a more effective control of the harmful fungus achieved because lower amounts of the individual active ingredients are required (synergism).
Für die erfindungsgemäßen Mischungen eignen sich alle in den eingangs angeführten Schriften angeführten Verbindungen des Typs IIA bzw. IIB.All of the mixtures at the outset are suitable for the mixtures according to the invention cited type IIA compounds or IIB.
Von besonderer Bedeutung sind dabei Verbindungen IIA und IIB,
in denen R" für eine der folgenden Gruppen steht:
RαRβC=NOCH2- oder RγON=CRδRε=NOCH2 wobei die Reste Rα, Rβ Rγ, Rδ und Rε im allgemeinen und im besonderen die in den folgenden Schriften beschriebenen Bedeutungen haben: EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575, EP-A 463 488, EP-A 472 300, EP-A 498 188, EP-A 498 396, EP-A 515 901, EP-A 585 751, WO-A 90/07,493, WO-A 92/13,830, WO-A 92/18,487, WO-A 92/18,494, WO-A 93/15,046, WO-A 93/16,986, WO-A 94/08,948, WO-A 94/08,968, JP-A 05/201,946, JP-A 05/255,012, JP-A 05/294,948, JP-A 06/025,133, JP-A 06/025,142, DE Pat. Anm. 44 03 447.., DE Pat. Anm. 44 03 448.., DE Pat. Anm. 44 21 180.5 und DE Pat. Anm. 44 21 182.1;
RαRβC = NOCH 2 - or RγON = CRδRε = NOCH 2 wherein the radicals Rα, Rβ Rγ, Rδ and Rε in general and in particular have the meanings described in the following documents: EP-A 370 629, EP-A 414 153, EP -A 426 460, EP-A 460 575, EP-A 463 488, EP-A 472 300, EP-A 498 188, EP-A 498 396, EP-A 515 901, EP-A 585 751, WO-A 90 / 07,493, WO-A 92 / 13,830, WO-A 92 / 18,487, WO-A 92 / 18,494, WO-A 93 / 15,046, WO-A 93 / 16,986, WO-A 94 / 08,948, WO-A 94 / 08,968, JP-A 05 / 201,946, JP-A 05 / 255,012, JP-A 05 / 294,948, JP-A 06 / 025,133, JP-A 06 / 025,142, DE Pat. Annotation 44 03 447 .., DE Pat. Note 44 03 448 .., DE Pat. Note 44 21 180.5 and DE Pat. Note 44 21 182.1;
Beispiele für insbesondere geeignete Wirkstoffe des Typs II sind
in den folgenden Tabellen zusammengestellt.
Bevorzugt setzt man bei der Bereitstellung der Mischungen die reinen Wirkstoffe I und IIA bzw. IIb ein, denen man je nach Bedarf weitere Wirkstoffe gegen Schädlinge (z.B. Insekten, Spinntiere oder Nematoden) oder Schadpilze oder auch herbizide oder wachstumsregulierende Wirkstoffe oder Düngemittel beimischen kann.It is preferred to use the when preparing the mixtures pure active ingredients I and IIA or IIb, which one depending on Need further active substances against pests (e.g. insects, arachnids or nematodes) or harmful fungi or herbicidal or add growth-regulating agents or fertilizers can.
Die Mischungen der Verbindungen I und IIA bzw. IIB bzw. die gleichzeitige gemeinsame oder getrennte Verwendung der Verbindungen I und IIA oder I und IIB zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum insbesondere von pflanzenpathogenen Pilzen aus. Sie sind z.T. systemisch wirksam (d.h. sie können bei der Anwendung zum Pflanzenschutz ohne Wirkungsverlust von der behandelten Pflanze aufgenommen und ggf. in der Pflanze transportiert werden) und können daher auch als Blatt- und Bodenfungizide eingesetzt werden.The mixtures of the compounds I and IIA or IIB or the simultaneous joint or separate use of the connections I and IIA or I and IIB are excellent Action against a wide range especially of phytopathogenic fungi. They are partly systemically effective (i.e. when used for crop protection without Loss of effectiveness absorbed by the treated plant and possibly transported in the plant) and can therefore also can be used as leaf and soil fungicides.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemüsepflanzen (z.B. Gurken, Bohnen und Kürbisgewächse), Gerste, Gras, Hafer, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, Weizen, Zierpflanzen, Zuckerrohr und einer Vielzahl von Samen.They are particularly important for combating a large number of mushrooms on various crops such as cotton, vegetables (e.g. cucumber, beans and pumpkin family), barley, grass, Oats, coffee, corn, fruit plants, rice, rye, soy, wine, Wheat, ornamental plants, sugar cane and a variety of seeds.
Insbesondere eignen sie sich zur Bekämpfung der folgenden pflanzenpathogenen Pilze: Erysiphe graminis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuckerrohr, Venturia inaequalis (Schorf) an Äpfeln, Helminthosporium-Arten an Getreide, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudocercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis, Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Arten in Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst sowie Fusarium- und Verticillium-Arten.In particular, they are suitable for combating the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, Podosphaera leucotricha on apples, Puccinia species on cereals, Rhizoctonia species on cotton, rice and Lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species Cereals, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae Rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, Pseudoperonospora species in hops and cucumbers, Alternaria species on vegetables and fruits as well as Fusarium and Verticillium species.
Sie sind außerdem im Materialschutz (z.B. Holzschutz) anwendbar, beispielsweise gegen Paecilomyces variotii.They can also be used in material protection (e.g. wood protection), for example against Paecilomyces variotii.
Die Verbindungen I und IIA bzw. I und IIB können gleichzeitig, und zwar gemeinsam oder getrennt oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungserfolg hat. The compounds I and IIA or I and IIB can simultaneously, namely applied together or separately or in succession be, the order in separate application in generally has no effect on the success of the control.
Die Verbindungen I und IIA werden üblicherweise in einem Gewichtsverhältnis von 10 : 1 bis 1 : 20, vorzugsweise 5 : 1 bis 1 : 3, insbesondere 3 : 1 bis 1 : 1 (I:IIA) angewendet.The compounds I and IIA are usually in one Weight ratio of 10: 1 to 1:20, preferably 5: 1 to 1: 3, in particular 3: 1 to 1: 1 (I: IIA) applied.
Die Verbindungen I und IIB werden üblicherweise in einem Gewichtsverhältnis von 10 : 1 bis 1 : 20, vorzugsweise 5 : 1 bis 1 : 3, insbesondere 3 : 1 bis 1 : 1 (I:IIB) angewendet.The compounds I and IIB are usually in one Weight ratio of 10: 1 to 1:20, preferably 5: 1 to 1: 3, in particular 3: 1 to 1: 1 (I: IIB) applied.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen je nach der Art des gewünschten Effektes bei 0,015 bis 10 kg/ha, vorzugsweise 0,1 bis 7 kg/ha, insbesondere 0,2 bis 3 kg/ha.The application rates of the mixtures according to the invention depend on the nature of the desired effect at 0.015 to 10 kg / ha, preferably 0.1 to 7 kg / ha, in particular 0.2 to 3 kg / ha.
Die Aufwandmengen liegen dabei für die Verbindungen I bei 0,005 bis 3 kg/ha, vorzugsweise 0,02 bis 2 kg/ha, insbesondere 0,05 bis 1 kg/ha.The application rates for the compounds I are 0.005 up to 3 kg / ha, preferably 0.02 to 2 kg / ha, in particular 0.05 to 1 kg / ha.
Die Aufwandmengen für die Verbindungen IIA liegen im allgemeinen bei 0,005 bis 5 kg/ha, vorzugsweise 0,01 bis 2 kg/ha, insbesondere 0,01 bis 1 kg/ha.The application rates for the compounds IIA are in general at 0.005 to 5 kg / ha, preferably 0.01 to 2 kg / ha, in particular 0.01 to 1 kg / ha.
Die Aufwandmengen für die Verbindungen IIB liegen im allgemeinen bei 0,005 bis 5 kg/ha, vorzugsweise 0,01 bis 2 kg/ha, insbesondere 0,01 bis 1 kg/ha.The application rates for the compounds IIB are in general at 0.005 to 5 kg / ha, preferably 0.01 to 2 kg / ha, in particular 0.01 to 1 kg / ha.
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 0,001 bis 0,1 g/kg Saatgut, vorzugsweise 0,002 bis 0,05 g/kg Saatgut, insbesondere 0,005 bis 0,5 g/kg Saatgut verwendet.When treating seeds, application rates are generally applied on a mixture of 0.001 to 0.1 g / kg of seed, preferably 0.002 up to 0.05 g / kg of seed, in particular 0.005 to 0.5 g / kg of seed used.
Sofern für Pflanzen pathogene Schadpilze zu bekämpfen sind erfolgt die gemeinsame oder getrennte Applikation der Verbindungen I und IIA bzw. I und IIB oder der Mischungen aus den Verbindungen I und IIA bzw. I und IIB durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Keimen der Pflanzen.If pathogenic harmful fungi are to be combated for plants the joint or separate application of the connections I and IIA or I and IIB or the mixtures of the compounds I and IIA or I and IIB by spraying or dusting the Seeds, plants or soils before or after sowing the plants or before or after the plants germinate.
Die erfindungsgemäßen fungiziden synergistischen Mischungen bzw. die Verbindungen I und IIA bzw. I und IIB können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen, Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten aufbereitet und durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsform ist abhängig vom Verwendungszweck; sie soll in jedem Fall eine möglichst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten. The fungicidal synergistic mixtures or the compounds I and IIA or I and IIB can for example in the form of directly sprayable solutions, powders and suspensions or in the form of high-proof aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, Pastes, dusts, spreading agents or granules prepared and by spraying, atomizing, dusting, scattering or Pouring can be applied. The form of application depends on Usage; in any case, it should be as fine and ensure uniform distribution of the mixture according to the invention.
Die Formulierungen werden in an sich bekannter Weise hergestellt, z.B. durch Zugabe von Lösungsmitteln und/oder Trägerstoffen. Den Formulierungen werden üblicherweise inerte Zusatzstoffe wie Emulgiermittel oder Dispergiermittel beigemischt.The formulations are prepared in a manner known per se, e.g. by adding solvents and / or carriers. The formulations are usually inert additives such as emulsifiers or dispersants.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali- und Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäure, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolether, Kondensationsprodukte von sulfoniertem Naphthalin und seinen Derivaten mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol oder Tributylphenylpolyglycolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Polyoxypropylen, Laurylalkoholpolyglycoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The alkali, alkaline earth and ammonium salts of aromatic sulfonic acids, e.g. Lignin-, Phenolic, naphthalene and dibutylnaphthalenesulfonic acid, as well as from Fatty acid, alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or Nonylphenol, alkylphenol or tributylphenyl polyglycol ether, Alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin sulfite liquors or methyl cellulose into consideration.
Pulver, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermahlen der Verbindungen I und IIA bzw. I und IIB oder der Mischungen aus den Verbindungen I und IIA bzw. I und IIB mit einem festen Trägerstoff hergestellt werden.Powders, materials for spreading and dusts can be mixed or combined Grinding of the compounds I and IIA or I and IIB or the mixtures of the compounds I and IIA or I and IIB with a solid carrier.
Granulate (z.B. Umhüllungs-, Imprägnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Trägerstoff hergestellt.Granules (e.g. coating, impregnation or homogeneous granules) are usually by binding the active ingredient or the active ingredients are produced on a solid carrier.
Als Füllstoffe bzw. feste Trägerstoffe dienen beispielsweise Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Kalzium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver und andere feste Trägerstoffe.Serve as fillers or solid carriers, for example Mineral soils such as silica gel, silicas, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers such as ammonium sulfate, Ammonium phosphate, ammonium nitrate, urea and vegetable Products such as flour, tree bark, wood and nutshell flour, Cellulose powder and other solid carriers.
Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.-% einer der Verbindungen IA bzw. IB, IIA oder IIB oder der Mischung aus den Verbindungen I und IIA bzw. I und IIB. The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of one of the compounds IA or IB, IIA or IIB or the mixture of the compounds I and IIA or I and IIB.
Die Wirkstoffe werden dabei in einer Reinheit von 90 % bis 100 %, vorzugsweise 95 % bis 100 % (nach 1H-NMR- oder HPLC-Spektrum) eingesetzt.The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to 1 H-NMR or HPLC spectrum).
Die Verbindungen I, IIA und IIB bzw. die Mischungen oder die entsprechenden Formulierungen werden angewendet, indem man die Schadpilze, ihren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen, Böden, Flächen oder Räume mit einer fungizid wirksamen Menge der Mischung bzw. der Verbindungen I und IIA oder I und IIB bei getrennter Ausbringung, behandelt. Die Behandlung kann vor oder nach dem Befall durch die Schadpilze erfolgen.The compounds I, IIA and IIB or the mixtures or the corresponding formulations are applied by the Harmful fungi, their habitat or those to be protected against fungal attack Materials, plants, seeds, soils, surfaces or spaces with a fungicidally effective amount of the mixture or compounds I and IIA or I and IIB when applied separately. Treatment can take place before or after infestation by the harmful fungi respectively.
Die synergistische Wirkung der erfindungsgemäßen Mischungen ließ sich durch die folgenden Versuche zeigen:The synergistic effect of the mixtures according to the invention was not are shown by the following experiments:
Die Versuche wurden mit den folgenden Verbindungen durchgeführt,
denen aus Gründen der Übersicht die Bezeichnungen (A), (B), (C)
und (D) zugeordnet wurden:
Paprikasämlinge der Sorte "Neusiedler Ideal Elite" wurden, nachdem sich 4 bis 5 Blätter gut entwickelt hatten, mit wäßrigen Suspensionen, die 80 % Wirkstoff und 20 % Emulgiermittel in der Trockensubstanz enthielten, tropfnaß gespritzt. Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer Konidienaufschwemmung des Pilzes Botrytis cinerea besprüht und bei 22 bis 24°C in eine Kammer mit hoher Luftfeuchtigkeit gestellt. Nach 5 Tagen hatte sich die Krankheit auf den unbehandelten Kontrollpflanzen so stark entwickelt, daß die entstandenen Blattnekrosen den überwiegenden Teil der Blätter bedeckten. Pepper seedlings of the variety "Neusiedler Ideal Elite" were after 4 to 5 leaves had developed well, with watery ones Suspensions containing 80% active ingredient and 20% emulsifier in the Contained dry substance, sprayed to runoff. After drying of the spray coating, the plants were exposed to a conidia of the fungus Botrytis cinerea and sprayed at 22 to 24 ° C in a chamber with high humidity. To The disease had remained on the untreated control plants for 5 days developed so strongly that the resulting leaf necrosis covered most of the leaves.
Die visuell ermittelten Werte für den Prozentanteil befallener Blattfläche wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel ermittelt (S. R. Colby "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, Seiten 20 bis 22 (1967)) und mit den beobachteten Wirkungsgraden verglichen.The visually determined values for the percentage of infested Leaf area were rated as efficiencies as% of the untreated control converted. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0% infestation. The too expected efficiencies for drug combinations have been postponed the Colby formula (S. R. Colby "Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds 15, Pages 20 to 22 (1967)) and with the observed efficiencies compared.
Versuchsergebnis: Der beobachtete Wirkungsgrad ist in allen Mischungsverhältnissen höher, als nach der Colby-Formel vorausberechnet.Test result: The observed efficiency is in all Mixing ratios higher than calculated using the Colby formula.
Scheiben von grünen Paprikaschoten wurden mit wäßriger Wirkstoffaufbereitung, die 80 % Wirkstoff und 20 % Emulgiermittel in der Trockensubstanz enthielt, tropfnaß besprüht. 2 Stunden nach dem Antrocknen des Spritzbelages wurden die Fruchtscheiben mit einer Sporensuspension von Botrytis cinerea, die 1,7 x 106 Sporen pro ml einer 2 %igen Biomalzlösung enthielt, inokuliert. Die inokulierten Fruchtscheiben wurden anschließend in feuchten Kammern bei 18°C für 4 Tage aufgestellt. Dann erfolgte visuell die Auswertung der Botrytis-Entwicklung auf den befallenen Fruchtscheiben.Slices of green peppers were sprayed to runoff point with aqueous active compound preparation which contained 80% active compound and 20% emulsifier in the dry substance. 2 hours after the spray coating had dried on, the fruit slices were inoculated with a spore suspension of Botrytis cinerea, which contained 1.7 × 10 6 spores per ml of a 2% biomalt solution. The inoculated fruit slices were then placed in moist chambers at 18 ° C for 4 days. Then the botrytis development was visually evaluated on the affected fruit slices.
Die visuell ermittelten Werte für den Prozentanteil befallener Blattfläche wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffkombinationen wurden nach der Colby-Formel ermittelt (S. R. Colby "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds 15, Seiten 20 bis 22 (1967)) und mit den beobachteten Wirkungsgraden verglichen.The visually determined values for the percentage of infested Leaf area were rated as efficiencies as% of the untreated control converted. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0% infestation. The too expected efficiencies for drug combinations have been postponed the Colby formula (S. R. Colby "Calculating synergistic and antagonistic responses of herbicide combinations ", Weeds 15, Pages 20 to 22 (1967)) and with the observed efficiencies compared.
Versuchsergebnis: Der beobachtete Wirkungsgrad ist in allen Mischungsverhältnissen höher, als nach der Colby-Formel vorausberechnet.Test result: The observed efficiency is in all Mixing ratios higher than calculated using the Colby formula.
Claims (10)
- A fungicidal mixture comprisingin a synergistically active amount.a) a p-hydroxyaniline derivative of the formula Iwhere the radicals have the following meanings:
- R1
- is hydrogen, C1-C8-alkyl which can be partially or
fully halogenated and/or can have attached to it one
or two of the following groups: C1-C4-alkoxy,
C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C7-cycloalkyl,
C5-C7-cycloalkenyl, it being possible for the cyclic
groups, in turn, to have attached to them one to
three halogen atoms, C1-C3-alkyl groups and/or
C1-C3-alkoxy groups, and aryl which can be partially
or fully halogenated and/or can have attached to it
one to three of the following substitutents: nitro,
cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy,
C1-C4-haloalkoxy and C1-C4-alkylthio;
C3-C6-cycloalkyl or C3-C6-cycloalkenyl, it being possible for these radicals to be partially or fully halogenated and/or to have attached to them one to five of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and aryl which can be partially or fully halogenated and/or can have attached to it one to three of the following substituents: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
C6-C15-bicycloalkyl or C7-C15-bicycloalkenyl, it being possible for these radicals to be partially or fully halogenated and/or to have attached to them one to five of the following groups: C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and aryl which can be partially or fully halogenated and/ or can have attached to it one to three of the following substituents: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio; - R2 and R3
- independently of one another are halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
- Z
- is H or R4-(CO)- where
- R4
- is C1-C6-alkyl or C2-C6-alkenyl, it being possible
for these groups to be partially or fully
halogenated and/or to have attached to them one
of the following radicals: C1-C4-alkoxy,
C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C7-cycloalkyl,
C5-C7-cycloalkenyl or aryl, it being possible
for the aromatic radicals, in turn, to
have attached to them one to three of the
following groups: nitro, cyano, halogen, C1-C4-alkyl,
C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy
and C1-C4-alkylthio;
C3-C7-cycloalkyl or C5-C7-cycloalkenyl, it being possible for these groups to have attached to them one to three of the following radicals: halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy;
aryl which can be partially or fully halogenated and/or can have attached to it one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
OR5 or NR6R7 where - R5
- is C1-C6-alkyl or C2-C6-alkenyl, it being
possible for these groups to be partially or
fully halogenated and/or to have attached to
them one of the following radicals:
C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C3-C7-cycloalkyl, C5-C7-cycloalkenyl or aryl, it being possible for the aromatic radicals, in turn, to have attached to them one to three of the following groups: nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
C3-C7-cycloalkyl or C5-C7-cycloalkenyl, it being possible for these groups to have attached to them one to three of the follow-ing radicals: halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy;
aryl, which can be partially or fully halo-genated and/or can have attached to it one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio; - R6
- is C1-C6-alkyl or C2-C6-alkenyl, it being
possible for these groups to be partially or
fully halogenated and/or to have attached to
them one of the following radicals:
C1-C4-alkylthio, C3-C7-cycloalkyl, C5-C7-cycloalkenyl or aryl, it being possible for the aromatic radicals, in turn, to have attached to them one to three of the following groups: nitro, cyano, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio;
C3-C7-cycloalkyl or C5-C7-cycloalkenyl, it being possible for these groups to have attached to them one to three of the following radicals: halogen, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy;
aryl which can be partially or fully halo-genated and/or can have attached to it one to three of the following radicals: nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyly C1-C4-alkoxy, C1-C4-haloalkoxy and C1-C4-alkylthio; and - R7
- is hydrogen or C1-C6-alkyl,
b) an active ingredient of the formula IIA or IIBwhere .... is a double or single bond and the index and the substituents have the following meanings:
- R'
- -C[CO2CH3]=CHOCH3, -C[CO2CH3]=NOCH3, -C[CONHCH3]=NOCH3, -C[CO2CH3]=CHCH3, -C[CO2CH3]=CHCH2CH3, -C[COCH3]=NOCH3, -C[COCH2CH3]=NOCH3, -N(OCH3)-CO2CH3, -N(CH3)-CO2CH3, -N(CH2CH3)-CO2CH3;
- R"
- is a C-organic radical which is bonded directly or
via an oxy, mercapto, amino or alkylamino group;
together with a group X and the ring Q or T to which it is bonded is an unsubstituted or substituted bicyclic, partially or fully unsaturated system which, besides carbon ring members, may contain hetero atoms from the group consisting of oxygen, sulfur and nitrogen; - Rx
- -OC[CO2CH3]=CHOCH3, -OC[CO2CH3]=CHCH3, -OC[CO2CH3]=CHCH2CH3, -SC[CO2CH3]=CHOCH3, -SC[CO2CH3]=CHCH3, -SC[CO2CH3]=CHCH2CH3, -N(CH3)C[CO2CH3]=CHOCH3, -N(CH3)C[CO2CH3]=NOCH3, -CH2C[CO2CH3]=CHOCH3, -CH2C[CO2CH3]=NOCH3, -CH2C[CONHCH3]=NOCH3;
- Ry
- is oxygen, sulfur, =CH- or =N-;
- n
- is 0, 1, 2 or 3, it being possible for the radicals X to be different when n > 1;
- x
- is cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl,
C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio;
in the event that n > 1, a C3-C5-alkylene, C3-C5-alkenylene, oxy-C2-C4-alkylene, oxy-C1-C3-alkyleneoxy, oxy-C2-C4-alkenylene, oxy-C2-C4-alkenyleneoxy or butadienediyl group which is bonded to two adjacent C atoms of the phenyl ring, it being possible for these chains, in turn, to have attached to them one to three of the following radicals: halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, - Y
- is =C- or -N-;
- Q
- is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridinyl, pyrimidinyl and triazinyl; and
- T
- is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl and triazinyl,
- A mixture as claimed in claim 1, wherein, in the compounds I as set forth in claim 1, Z is hydrogen.
- A mixture as claimed in claim 2, wherein the compound I as set forth in claim 1 is a compound from the table which follows:
- A mixture as claimed in any of claims 1 to 3, wherein the compound IIA as set forth in claim 1, where Q is phenyl and n is zero, is a compound from the table which follows:
R' R'' -C(CO2CH3)=CHOCH3 2-CH3-C6H4-OCH2 -C(CO2CH3)=CHOCH3 2,5-(CH3)2-C6H3-OCH2 -C(CO2CH3)=CHOCH3 2-CH2CH2CH3, 6-CF3-pyrimidin-4-yl -C(CO2CH3)=CHOCH3 C6H5-O -C(CO2CH3)=CHOCH3 6-[2-CN-C6H4-O]-pyrimidin-4-yl -C(CO2CH3)=CHOCH3 3-CF3-C6H4-C(CH3)=N-OCH2 -C(CO2CH3)=CHOCH3 CH3O-N=C(4-Cl-C6H4)-C(CH3)=N-OCH2 -C(CO2CH3)=CHOCH3 2-CH3-C6H4-OCH2 -C(CO2CH3)=CHOCH3 2.5-(CH3)2-C6H3-OCH2 -C(CO2CH3)=CHOCH3 3-CF3-C6H4-C(CH3)=N-OCH2 -C(CO2CH3)=CHOCH3 2-CH3-C6H4-OCH2 -C(CO2CH3)=CHOCH3 2.5-(CH3)2-C6H3-OCH2 -C(CO2CH3)=CHOCH3 1-(4-Cl-C6H4)-pyrazol-3-yl-OCH2 -C(CO2CH3)=CHOCH3 3-CF3-C6H4-C(CH3)=N-OCH2 -C(CO2CH3)=CHOCH3 CH3O-N=C(4-Cl-C6H4)-C(CH3)=N-OCH2 -N(OCH3)-CO2CH3 2-CH3-C6H4-OCH2 -N(OCH3)-CO2CH3 2.5-(CH3)2-C6H4-OCH2 -N(OCH3)-CO2CH3 1-(4-Cl-C6H4)-pyrazol-3-yl-OCH2 -N(OCH3)-CO2CH3 3.5-Cl2-C6H3-C(CH3)=N-OCH2 - A fungicidal mixture as claimed in any of claims 1 to 4, wherein the weight ratio of the compound I to the compound IIA or IIB is 20:1 to 0.05:1.
- A method of controlling harmful fungi, which comprises treating the harmful fungi, their environment, or the plants, seeds, soils, areas, materials or spaces to be kept free from them, with a compound of the formula I as set forth in claim 1 and a compound of the formula IIA or IIB as set forth in claim 1.
- A method as claimed in claim 6, wherein the compound I as set forth in claim 1 and the compound IIA or IIB as set forth in claim 1 are applied simultaneously, namely together or separately, or in succession.
- A method as claimed in claim 6 or 7, wherein the compound I as set forth in claim 1 is applied in an amount of 0.05 to 1 kg/ha.
- A method as claimed in any of claims 6 to 8, wherein the compound IIA or IIB as set forth in claim 1 is applied in an amount of 0.01 to 1 kg/ha.
- The use of the compound I as set forth in any of claims 1 to 3 for the preparation of a fungicidally active synergistic mixture as claimed in any of claims 1 to 4.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19543746 | 1995-11-24 | ||
| DE19543746A DE19543746A1 (en) | 1995-11-24 | 1995-11-24 | Fungicidal agents |
| PCT/EP1996/005064 WO1997019595A1 (en) | 1995-11-24 | 1996-11-18 | Fungicidal mixture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0863702A1 EP0863702A1 (en) | 1998-09-16 |
| EP0863702B1 true EP0863702B1 (en) | 2001-08-16 |
Family
ID=7778260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96939086A Expired - Lifetime EP0863702B1 (en) | 1995-11-24 | 1996-11-18 | Fungicidal mixture |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0863702B1 (en) |
| JP (1) | JP2000510437A (en) |
| KR (1) | KR100428275B1 (en) |
| CN (1) | CN1214717C (en) |
| AR (1) | AR004744A1 (en) |
| AT (1) | ATE204127T1 (en) |
| AU (1) | AU729337B2 (en) |
| BR (1) | BR9611631A (en) |
| CA (1) | CA2235039C (en) |
| CO (1) | CO4770920A1 (en) |
| CZ (1) | CZ293592B6 (en) |
| DE (2) | DE19543746A1 (en) |
| DK (1) | DK0863702T3 (en) |
| ES (1) | ES2163046T3 (en) |
| IL (1) | IL123896A (en) |
| MX (1) | MX9803080A (en) |
| NZ (1) | NZ322502A (en) |
| PT (1) | PT863702E (en) |
| SK (1) | SK282770B6 (en) |
| UA (1) | UA52631C2 (en) |
| WO (1) | WO1997019595A1 (en) |
| ZA (1) | ZA969796B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2843277A1 (en) | 2013-09-02 | 2015-03-04 | Johnson Electric S.A. | Gas shut-off valve |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA59381C2 (en) | 1996-12-13 | 2003-09-15 | Баєр Акціенгезельшафт | Plant protection agents |
| GB9718366D0 (en) * | 1997-08-29 | 1997-11-05 | Ciba Geigy Ag | Novel combinations |
| UA70327C2 (en) * | 1998-06-08 | 2004-10-15 | Баєр Акціенгезельшафт | Method of combating phytopathogenic diseases on crop plants and a fungicidal composition |
| GB0127556D0 (en) | 2001-11-16 | 2002-01-09 | Syngenta Participations Ag | Organic compounds |
| CN103355298B (en) * | 2012-03-29 | 2016-04-06 | 陕西韦尔奇作物保护有限公司 | A kind of bactericidal composition containing fenhexamid and antibiotics |
| EP3047731A1 (en) | 2015-01-21 | 2016-07-27 | Basf Se | Method for combating soybean rust comprising treating soybean with (2E)-2-[3-substituted-2 [[(E)-[(2E)-2-alkoxyimino-1-methyl-2-phenyl-ethylidene]amino]oxymethyl]phenyl]-2-methoxy-imino-N-methyl-acetamides |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4313867A1 (en) * | 1993-04-28 | 1994-11-03 | Bayer Ag | Fungicidal active ingredient combinations |
| US6518304B1 (en) * | 1993-12-02 | 2003-02-11 | Sumitomo Chemical Company, Limited | Fungicidal composition |
| JPH07304607A (en) * | 1994-05-13 | 1995-11-21 | Sumitomo Chem Co Ltd | Germicidal composition |
| AU688540B2 (en) * | 1994-07-21 | 1998-03-12 | Basf Aktiengesellschaft | Method of combating harmful fungi |
| DE4437048A1 (en) * | 1994-10-17 | 1996-04-18 | Bayer Ag | Fungicidal active ingredient combinations |
| HUP9800262A3 (en) * | 1995-02-11 | 2000-06-28 | Basf Ag | Fungicide |
-
1995
- 1995-11-24 DE DE19543746A patent/DE19543746A1/en not_active Withdrawn
-
1996
- 1996-11-18 DE DE59607515T patent/DE59607515D1/en not_active Expired - Fee Related
- 1996-11-18 ES ES96939086T patent/ES2163046T3/en not_active Expired - Lifetime
- 1996-11-18 EP EP96939086A patent/EP0863702B1/en not_active Expired - Lifetime
- 1996-11-18 JP JP09520132A patent/JP2000510437A/en not_active Ceased
- 1996-11-18 AU AU76268/96A patent/AU729337B2/en not_active Ceased
- 1996-11-18 AT AT96939086T patent/ATE204127T1/en not_active IP Right Cessation
- 1996-11-18 IL IL12389696A patent/IL123896A/en not_active IP Right Cessation
- 1996-11-18 BR BR9611631A patent/BR9611631A/en not_active IP Right Cessation
- 1996-11-18 UA UA98063277A patent/UA52631C2/en unknown
- 1996-11-18 CZ CZ19981610A patent/CZ293592B6/en not_active IP Right Cessation
- 1996-11-18 CA CA002235039A patent/CA2235039C/en not_active Expired - Fee Related
- 1996-11-18 KR KR10-1998-0703866A patent/KR100428275B1/en not_active IP Right Cessation
- 1996-11-18 DK DK96939086T patent/DK0863702T3/en active
- 1996-11-18 SK SK507-98A patent/SK282770B6/en unknown
- 1996-11-18 WO PCT/EP1996/005064 patent/WO1997019595A1/en active IP Right Grant
- 1996-11-18 PT PT96939086T patent/PT863702E/en unknown
- 1996-11-18 CN CNB961985062A patent/CN1214717C/en not_active Expired - Fee Related
- 1996-11-18 NZ NZ322502A patent/NZ322502A/en unknown
- 1996-11-22 AR ARP960105297A patent/AR004744A1/en unknown
- 1996-11-22 ZA ZA9609796A patent/ZA969796B/en unknown
- 1996-11-22 CO CO96061695A patent/CO4770920A1/en unknown
-
1998
- 1998-04-20 MX MX9803080A patent/MX9803080A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2843277A1 (en) | 2013-09-02 | 2015-03-04 | Johnson Electric S.A. | Gas shut-off valve |
| DE102013109570A1 (en) | 2013-09-02 | 2015-03-19 | Johnson Electric Germany GmbH & Co. KG | Gasabschaltventil |
Also Published As
| Publication number | Publication date |
|---|---|
| IL123896A0 (en) | 1998-10-30 |
| DE59607515D1 (en) | 2001-09-20 |
| DE19543746A1 (en) | 1997-05-28 |
| CN1214717C (en) | 2005-08-17 |
| WO1997019595A1 (en) | 1997-06-05 |
| CA2235039C (en) | 2005-01-18 |
| SK50798A3 (en) | 1998-12-02 |
| JP2000510437A (en) | 2000-08-15 |
| IL123896A (en) | 2004-06-01 |
| AU729337B2 (en) | 2001-02-01 |
| BR9611631A (en) | 1999-05-25 |
| KR19990071590A (en) | 1999-09-27 |
| DK0863702T3 (en) | 2001-10-08 |
| ZA969796B (en) | 1998-05-22 |
| MX9803080A (en) | 1998-11-30 |
| CA2235039A1 (en) | 1997-06-05 |
| CZ161098A3 (en) | 1998-10-14 |
| EP0863702A1 (en) | 1998-09-16 |
| AU7626896A (en) | 1997-06-19 |
| AR004744A1 (en) | 1999-03-10 |
| KR100428275B1 (en) | 2005-01-15 |
| NZ322502A (en) | 1999-01-28 |
| ATE204127T1 (en) | 2001-09-15 |
| ES2163046T3 (en) | 2002-01-16 |
| PT863702E (en) | 2002-02-28 |
| SK282770B6 (en) | 2002-12-03 |
| CZ293592B6 (en) | 2004-06-16 |
| UA52631C2 (en) | 2003-01-15 |
| CO4770920A1 (en) | 1999-04-30 |
| CN1202798A (en) | 1998-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0772398B1 (en) | Method of combating harmful fungi | |
| EP1039803B1 (en) | Fungicide mixtures based on amide compounds | |
| EP0923289B1 (en) | Fungicidal mixtures | |
| EP1039800B1 (en) | Fungicide mixtures based on pyridine carboxamide compounds | |
| EP0910948B1 (en) | Fungicidal mixture | |
| EP1228691A2 (en) | Fungicidal mixtures based on pyridine carboxamide compounds | |
| EP0863702B1 (en) | Fungicidal mixture | |
| WO1996032015A1 (en) | Synergistic fungicide compositions made of quinoline derivatives and cytochrom b/c inhibitors | |
| EP0900009B1 (en) | Fungicide mixtures | |
| EP0906017B1 (en) | Fungicide mixtures | |
| EP0900008B1 (en) | Fungicidal mixtures | |
| EP1214881B1 (en) | Fungicidal mixtures based upon amid compounds | |
| EP0765118B1 (en) | Fungicidal mixtures | |
| WO1998041094A1 (en) | Fungicide mixture | |
| EP0900013B1 (en) | Fungicide mixtures | |
| EP0912088B1 (en) | Fungicidal mixtures | |
| EP1214882B1 (en) | Fungicidal mixtures based upon amid compounds | |
| EP0892603B1 (en) | Fungicidal mixtures | |
| EP0763975B1 (en) | Fungicidal mixtures | |
| EP0900012A1 (en) | Fungicide mixtures | |
| DE10252657A1 (en) | Synergistic, broad-spectrum fungicidal mixture, useful for protection of plants, especially against true mildews, contains benzamidoxime derivative and cyprodinil and/or proquinazid | |
| EP0900014A1 (en) | Fungicide mixtures |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19980325 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB IT LI NL PT SE |
|
| 17Q | First examination report despatched |
Effective date: 20000627 |
|
| GRAG | Despatch of communication of intention to grant |
Free format text: ORIGINAL CODE: EPIDOS AGRA |
|
| GRAG | Despatch of communication of intention to grant |
Free format text: ORIGINAL CODE: EPIDOS AGRA |
|
| GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
| GRAH | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOS IGRA |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE CH DE DK ES FR GB IT LI NL PT SE |
|
| REF | Corresponds to: |
Ref document number: 204127 Country of ref document: AT Date of ref document: 20010915 Kind code of ref document: T |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: NV Representative=s name: SCHMAUDER & PARTNER AG PATENTANWALTSBUERO Ref country code: CH Ref legal event code: EP |
|
| REF | Corresponds to: |
Ref document number: 59607515 Country of ref document: DE Date of ref document: 20010920 |
|
| REG | Reference to a national code |
Ref country code: DK Ref legal event code: T3 |
|
| GBT | Gb: translation of ep patent filed (gb section 77(6)(a)/1977) |
Effective date: 20011003 |
|
| REG | Reference to a national code |
Ref country code: GB Ref legal event code: IF02 |
|
| ET | Fr: translation filed | ||
| REG | Reference to a national code |
Ref country code: ES Ref legal event code: FG2A Ref document number: 2163046 Country of ref document: ES Kind code of ref document: T3 |
|
| REG | Reference to a national code |
Ref country code: PT Ref legal event code: SC4A Free format text: AVAILABILITY OF NATIONAL TRANSLATION Effective date: 20011116 |
|
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
| 26N | No opposition filed |
Opponent name: APPLIED RESEARCH SYSTEMS ARS HOLDING N.V. |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 20071104 Year of fee payment: 12 Ref country code: ES Payment date: 20071219 Year of fee payment: 12 Ref country code: DK Payment date: 20071115 Year of fee payment: 12 Ref country code: DE Payment date: 20071115 Year of fee payment: 12 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: AT Payment date: 20071113 Year of fee payment: 12 Ref country code: IT Payment date: 20071123 Year of fee payment: 12 Ref country code: CH Payment date: 20071114 Year of fee payment: 12 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 20071106 Year of fee payment: 12 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: GB Payment date: 20071114 Year of fee payment: 12 Ref country code: FR Payment date: 20071108 Year of fee payment: 12 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: PT Payment date: 20071106 Year of fee payment: 12 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: BE Payment date: 20071130 Year of fee payment: 12 |
|
| REG | Reference to a national code |
Ref country code: PT Ref legal event code: MM4A Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20090518 |
|
| BERE | Be: lapsed |
Owner name: *BASF A.G. Effective date: 20081130 |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
| REG | Reference to a national code |
Ref country code: DK Ref legal event code: EBP |
|
| EUG | Se: european patent has lapsed | ||
| GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20081118 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090601 |
|
| NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee |
Effective date: 20090601 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: PT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090518 Ref country code: IT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081118 Ref country code: AT Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081118 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST Effective date: 20090731 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081130 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081130 Ref country code: DK Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081130 Ref country code: DE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20090603 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081130 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081118 |
|
| REG | Reference to a national code |
Ref country code: ES Ref legal event code: FD2A Effective date: 20081119 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: ES Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081119 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081119 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20081130 |